tert-Butyl hydroperoxide → 2-Cyclopenten-1-one

HRID 444318Notes

Reaction equation

HRID 444318 reaction equation
[C:1]([O:5]O)(C)([CH3:3])[CH3:2].[CH:7]1[CH2:11][CH2:10][CH2:9][CH:8]=1>>[CH:1]1([OH:5])[CH2:3][CH2:8][CH:7]=[CH:2]1.[C:7]1(=[O:5])[CH2:11][CH2:10][CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 8882Cyclopentene

Product 2

HCID 135882-Cyclopenten-1-oneYield 10%HCID 2201642-Cyclopentene-1-ol

Procedure

East German Pat. No. 81650 issued on May 5, 1971 discloses the use of Rh(Pφ3)3Cl and a large amount of t-butyl hydroperoxide (with oxygen) for the oxidation of cyclopentene at 45° C. This reaction was slow giving 2-cyclopentenol in 7% yield along with 10% of 2-cyclopentenone.

Workup

  1. customat 45° C

Sources & evidence

ORD record
ord-34e37f845f534495a0551a57745f15b8
Source dataset
uspto-grants-1981_04
Patent number
US04263447

Reaction notes

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